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Ethylene Glycol → Ethyl acetate hexane

HRID 443031
Notes
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Reaction equation

HRID 443031 reaction equation
Cl.[CH:2]1[C:15]2[C:6](=[N:7][C:8]3[C:13]([C:14]=2NNS(C2C=C[C:24]([CH3:27])=CC=2)(=O)=O)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1.[OH-:28].[Na+].[CH2:30]([OH:33])[CH2:31][OH:32]>O>[CH3:31][O:32][C:5]1[C:6]2[C:15](=[CH:14][C:13]3[C:8]([N:7]=2)=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:2]=[CH:3][CH:4]=1.[CH3:14][CH2:15][CH2:2][CH2:3][CH2:4][CH3:5].[C:30]([O:33][CH2:24][CH3:27])(=[O:28])[CH3:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 86753010N1-9-acridinyl-N2-p-toluenesulfonylhydrazine hydrochloride

Product 2

HCID 122924034-MethoxyacridineHCID 21226206Ethyl acetate hexaneYield 95.2%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A mixed solution comprising 124 mg of N1 -9-(4-methoxy)acridinyl-N2 -p-toluenesulfonylhydrazine hydrochloride (18), 40 mg of sodium hydroxide, and 5 ml of ethylene glycol was allowed to react at 100° C. for a period of one hour. After the completion of the reaction, the reacted solution was introduced into water and the product was extracted by ethyl acetate. After ethyl acetate was distilled away, the residue was purified by column chromatography and 57.6 mg of 4-methoxyacridine (19) was obtained as crystals on recrystallization by hexane-ethyl acetate (yield 95.2%).

Workup

  1. customto react at 100° C. for a period of one hour
  2. customAfter the completion of the reaction
  3. extractionthe product was extracted by ethyl acetate
  4. distillationAfter ethyl acetate was distilled away
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-cabcf734a9004042a5c08e9c599f56bb
Source dataset
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05892042

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes